CN113444072A - Compound and application thereof - Google Patents

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CN113444072A
CN113444072A CN202010221174.6A CN202010221174A CN113444072A CN 113444072 A CN113444072 A CN 113444072A CN 202010221174 A CN202010221174 A CN 202010221174A CN 113444072 A CN113444072 A CN 113444072A
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CN113444072B (en
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李之洋
张辉
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula I. The compound provided by the invention takes a benzocarbazole group as a main structure, an arylamine structure and a specific electricity-absorbing group are introduced, the fixed combination can be beneficial to the balance of the transmission of holes and electrons, and when the compound is applied to an OLED device, the efficiency of the device can be effectively improved, and the driving voltage can be reduced.

Description

Compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
In recent years, Organic Light Emitting Diodes (OLEDs) have been developed very rapidly, and have a place in the field of information display, which is mainly benefited from the fact that OLED devices can prepare full-color display devices using three primary colors of high saturation, red, green and blue, and can realize bright, light, thin and soft colors without additional backlight sources.
The Organic Light Emitting Diode (OLED) device plays an important role in a thin-layer structure containing various organic functional materials, and common organic functional materials comprise a light emitting layer material, an electron blocking layer material, an electron transport layer material, a hole blocking layer material, a hole transport layer material and the like. After the power is switched on, electrons and holes are respectively injected and transmitted to the light-emitting layer and are recombined to generate excitons, so that light is emitted. Therefore, the research on organic functional materials in OLED devices is a key research topic for those skilled in the art.
At present, researchers have developed various organic functional materials for various specific device structures, which play roles in improving carrier mobility, regulating carrier balance, breaking through electroluminescence efficiency, and delaying device attenuation.
Conventional fluorescent emitters emit light primarily using singlet excitons generated upon recombination of holes and electrons, and such emitters are still used in various OLED devices. In addition, a phosphorescent emitter, that is, a material which can emit light by using both triplet excitons and singlet excitons, such as an iridium complex or the like, is also included. The thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve higher luminous efficiency without using a metal complex by promoting the conversion of triplet excitons to singlet excitons. The thermal excitation sensitization fluorescence (TASF) technology is to adopt TADF material to sensitize the luminophor in an energy transfer mode, so that higher luminous efficiency is realized, and the TADF material has wide application prospect in the OLED field.
Although various organic functional layer materials have been developed, nowadays, the requirements of people on the performance of the OLED device are higher and higher, and the existing organic functional materials cannot be applied to new OLED devices with higher performance.
Therefore, there is a need in the art to develop a wider variety of organic functional materials, which can improve the light emitting efficiency, reduce the driving voltage, and prolong the service life when applied to OLED devices.
Disclosure of Invention
An object of the present invention is to provide a compound capable of improving light emitting efficiency and reducing driving voltage when applied to an OLED device.
In order to achieve the purpose, the invention adopts the following technical scheme:
a compound having the structure shown in formula I;
Figure BDA0002426106780000021
in formula I: l is1And L2Each independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
Ar2and Ar3Each independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
R1and R2Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar1is the structure of a1 as follows:
Figure BDA0002426106780000022
in formula a1: x1-X8Selected from the group consisting of CR3Or N, R3Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, two adjacent R groups3May be fused to form a ring.
When the substituent group exists in the groups, the substituent group is selected from one or the combination of at least two of halogen, cyano, carbonyl, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 monocyclic aryl or condensed ring aryl, C3-C30 monocyclic heteroaryl or condensed ring heteroaryl.
The above "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from different substituents.
In the above substituents, the number of carbon atoms of the chain alkyl group having from C1 to C10 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, or the like; the carbon number of the C3-C10 cycloalkyl group can be C4, C5, C6, C7, C8, C9, C10 and the like; the C1-C10 alkoxy group may have C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the C1-C10 thioalkoxy group may have C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the C6-C30 monocyclic aryl group may have C10, C12, C14, C16, C18, C20, C26, C28 and the like; the number of carbons of the C10-C30 condensed ring aryl group may be C10, C12, C14, C16, C18, C20, C26, C28, etc.; the C3-C30 monocyclic heteroaryl group may have C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, etc.; the carbon number of the C6-C30 fused ring heteroaryl can be C10, C12, C14, C16, C18, C20, C26, C28 and the like. The number of carbons is merely an example and is not limited to the above.
In the present invention, the heteroatom of heteroaryl is generally referred to as N, O, S.
The atomic names given in this disclosure, including their respective isotopes, for example, hydrogen (H) includes1H (protium or H),2H (deuterium or D), etc.; carbon (C) then comprises12C、13C and the like.
In the present invention, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linkage can be formed.
Further preferably, Ar1A structure selected from the group consisting of a1-1 or a 1-2:
Figure BDA0002426106780000031
in the formula a1-1 or a1-2, the X3-X8Is as defined in formula a 1;
further preferably, X is3-X8Are both CH.
Still more preferably, Ar1Selected from the structures of formula a1-3 or a1-4 as follows:
Figure BDA0002426106780000032
in the formula a1-3 or a1-4, R3And X3-X6Is as defined in formula a 1; preferably, R3Selected from the group consisting of substituted or unsubstituted structural formulas:
Figure BDA0002426106780000041
further preferably, X is3-X6Are both CH.
The compounds of formula I of the present invention are preferably those of the following formulae I-1, I-2 or I-3:
Figure BDA0002426106780000042
in I-1, I-2 and I-3, the L1、L2、Ar1、Ar2、Ar3、R1And R2Are as defined in formula I.
Further preferably, in said formulae I, I-1, I-2 and I-3:
L1selected from single bonds orSubstituted or unsubstituted one of the following groups: phenylene, naphthylene, pyridylene, biphenylene;
L2selected from a single bond or one of the following substituted or unsubstituted groups: phenylene, naphthylene, pyridylene, biphenylene, dibenzofuran, dibenzothiophene;
Ar2and Ar3Each independently selected from one of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, dibenzofuran, dibenzothiophene, carbazolyl.
Further preferably, R is as defined above1、R2And R3Each independently selected from hydrogen or the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, etc., p-o, etc Dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinylA group selected from the group consisting of a phenyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a1, 5-diazananthyl group, a2, 7-diazpyrenyl group, a2, 3-diazananyl group, a1, 6-diazananyl group, a1, 8-diazananyl group, a 4,5,9, 10-tetraazaperyl group, a pyrazinyl group, a phenazinyl group, a phenothiazinyl group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbazinyl group, a phenanthrolinyl group, a1, 2, 3-triazolyl group, a1, 2, 4-triazolyl group, a benzotriazolyl group, a1, 2, 3-oxadiazolyl group, a1, 2, 5-oxadiazolyl group, a1, 2, 4-thiadiazolyl group, a1, 2, 5-thiadiazolyl group, a1, 3, 4-thiadiazolyl group, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of two of the foregoing.
Most preferably, said R1And R2Each independently selected from hydrogen.
Further, the compounds described by the general formula of the present invention may preferably be compounds of the following specific structures, which are merely representative:
Figure BDA0002426106780000061
Figure BDA0002426106780000071
Figure BDA0002426106780000081
Figure BDA0002426106780000091
Figure BDA0002426106780000101
Figure BDA0002426106780000111
Figure BDA0002426106780000121
Figure BDA0002426106780000131
Figure BDA0002426106780000141
Figure BDA0002426106780000151
Figure BDA0002426106780000161
Figure BDA0002426106780000171
Figure BDA0002426106780000181
Figure BDA0002426106780000191
Figure BDA0002426106780000201
Figure BDA0002426106780000211
as another aspect of the present invention, there is also provided a use of the compound as described above in an organic electroluminescent device. In particular, the application as a material for a light-emitting functional layer in an organic electroluminescent device is preferred. Preferably as a material in the light-emitting layer in the light-emitting functional layer, most preferably as a light-emitting host material in the light-emitting layer.
As still another aspect of the present invention, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layer contains therein a compound represented by each general formula as described above or a compound represented by each specific structural formula as described above.
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and a first electrode, a plurality of light-emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, wherein the hole injection transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is arranged between the hole transport region and the electron transport region; wherein, the luminous layer contains the compounds shown in the general formulas or the specific structural formulas.
The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives including compounds shown below as HT-1 to HT-34; or any combination thereof.
Figure BDA0002426106780000221
Figure BDA0002426106780000231
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI-1 to HI-3 described below.
Figure BDA0002426106780000241
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
Figure BDA0002426106780000242
Figure BDA0002426106780000251
The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.
Figure BDA0002426106780000252
Figure BDA0002426106780000261
Figure BDA0002426106780000271
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following: liq, LiF, NaCl, CsF, Li2O、Cs2CO3、BaO、Na、Li、Ca。
The cathode is metal, metal mixture or oxide such as magnesium silver mixture, LiF/Al, ITO, etc.
The specific reason why the above-mentioned compound of the present invention is excellent as a material for a light-emitting layer in an organic electroluminescent device is not clear, and the following reason is presumed:
the compound provided by the invention takes benzocarbazole as a mother-core structure, adopts a specific arylamine structure and an electricity-absorbing group for combination and collocation, and aims to ensure the corresponding HOMO energy level of the benzocarbazole, has larger conjugation and plane type compared with the carbazole structure, provides good hole transmission capability, balances the transmission of holes and electrons through specific arylamine bridging substitution and the combination of an electricity-absorbing part, enables the composite center of a light-emitting layer to be closer to the middle, and finally shows more excellent performance in a device. When the compound is applied to an OLED device, the efficiency of the device can be effectively improved, and the driving voltage can be reduced.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples. The method and materials for obtaining the compound are not limited to the synthetic methods and materials used in the invention, and other methods or routes can be selected by those skilled in the art to obtain the novel compound provided by the invention. The compounds of the present invention, for which no synthetic method is mentioned, are commercially available starting products or are prepared by the starting products according to known methods.
The synthesis of the compounds of the present invention is briefly described below. The compounds of the invention of the general formula I can be synthesized by reference to the following synthetic route:
Figure BDA0002426106780000281
the above symbols all have the same meaning as in formula I. Wherein X represents halogen, Z1 represents boronic acid pinacol ester, and Z2 represents halogen.
Compounds of synthetic methods not mentioned in the following synthetic examples of the present invention are all commercially available starting products. The solvents and reagents used in the present invention, such as methylene chloride, ethanol, 1, 8-dibromonaphthalene, phenylboronic acid, carbazole, and other chemical reagents, are commercially available from the national chemical product markets, such as from national drug group reagents, TCI, Shanghai Bide pharmaceuticals, and Bailingwei reagents. In addition, they can be synthesized by a known method by those skilled in the art.
Synthesis example 1
Synthesis of Compound A1
Figure BDA0002426106780000291
Adding 2-bromo-5H benzo [ b ] carbazole (10mmol), 2-chloro-4-phenylquinazoline (10mmol), potassium carbonate (20mmol) and DMF200mL into a reaction bottle, heating to 150 ℃ for reaction for 4H, monitoring by TLC to complete reaction, cooling, adding water, filtering and drying to obtain A1-1.
Adding A1-1(6mmol), diphenylamine (6mmol), sodium tert-butoxide (10mmol), tris (dibenzylideneacetone) dipalladium (0.1mmol), tri-tert-butylphosphine (0.2mmol) and xylene 150mL into a reaction bottle, heating to 150 ℃ for reacting for 8h, monitoring the reaction by TLC, cooling, adding water and dichloromethane, separating an organic phase, concentrating, and purifying by column chromatography to obtain the compound A1.
Synthesis example 2:
synthesis of Compound A25
The difference from synthesis example 1 is that 2-chloro-4-phenylquinazoline was replaced with an equivalent amount of 2- (4-fluorophenyl) -4-chloroquinazoline to obtain compound a 25.
Synthesis example 3:
synthesis of Compound A33
Figure BDA0002426106780000292
Adding A1-1(10mmol), S1(10mmol), potassium carbonate (20mmol), tetrakis (triphenylphosphine) palladium (0.1mmol), 50mL of water and 200mL of dioxane into a reaction bottle, heating to 120 ℃ for reaction for 6h, monitoring the reaction completion by TLC, adding water and dichloromethane after cooling, separating an organic phase, concentrating, and purifying by column chromatography to obtain the compound A33.
Synthesis example 4:
synthesis of Compound C2
Figure BDA0002426106780000301
Adding 11-chloro-5H benzo [ b ] carbazole (10mmol), 2-chloro-4-phenylquinazoline (10mmol), potassium carbonate (20mmol) and DMF200mL into a reaction bottle, heating to 150 ℃ for reaction for 4H, monitoring by TLC to complete reaction, cooling, adding water, filtering and drying to obtain C2-1.
Adding C2-1(6mmol), S2(6mmol), sodium tert-butoxide (10mmol), tris (dibenzylideneacetone) dipalladium (0.1mmol), tri-tert-butylphosphine (0.2mmol) and 150mL of xylene into a reaction bottle, heating to 150 ℃ for reaction for 12h, monitoring the reaction by TLC, cooling, adding water and dichloromethane, separating an organic phase, concentrating, and purifying by column chromatography to obtain the compound C2.
Synthesis example 5:
synthesis of Compound C25
The difference from Synthesis example 4 was that 2-chloro-4-phenylquinazoline was replaced with an equivalent amount of 2- (4-fluorophenyl) -4-chloroquinazoline, and S2 was replaced with an equivalent amount of diphenylamine to give Compound C25.
Synthesis example 6:
synthesis of Compound D1
The difference from Synthesis example 1 is that 2-chloro-4-phenylquinazoline was replaced with an equivalent amount of 2-chloro-3-phenylquinoxaline to obtain compound D1.
Synthesis example 7:
synthesis of Compound D21
The difference from Synthesis example 3 was that 2-chloro-4-phenylquinazoline was replaced with an equivalent amount of 2-chloro-3-phenylquinoxaline, and S1 was replaced with an equivalent amount of triphenylamine-4-boronic acid to obtain Compound D21.
Synthesis example 8:
synthesis of Compound D26
Figure BDA0002426106780000311
Adding 4-chloro-5H benzo [ b ] carbazole (10mmol), 2-chloro-3-phenyl quinoxaline (10mmol), potassium carbonate (20mmol) and DMF200mL into a reaction flask, heating to 150 ℃ for reaction for 4H, monitoring by TLC to complete the reaction, cooling, adding water, filtering and drying to obtain D26-1.
Adding D26-1(6mmol), S2(6mmol), sodium tert-butoxide (10mmol), tris (dibenzylideneacetone) dipalladium (0.1mmol), tri-tert-butylphosphine (0.2mmol) and 150mL of xylene into a reaction bottle, heating to 150 ℃ for reaction for 12h, monitoring the reaction by TLC, cooling, adding water and dichloromethane, separating an organic phase, concentrating, and purifying by column chromatography to obtain a compound D26.
Synthesis example 9:
synthesis of Compound D72
Figure BDA0002426106780000312
Adding 11-chloro-5H benzo [ b ] carbazole (10mmol), 2-chloro-3-phenyl quinoxaline (10mmol), potassium carbonate (20mmol) and DMF200mL into a reaction flask, heating to 150 ℃ for reaction for 4H, monitoring by TLC to complete the reaction, cooling, adding water, filtering and drying to obtain D72-1.
Adding D72-1(6mmol), S3(6mmol), potassium carbonate (12mmol), tetrakis (triphenylphosphine) palladium (0.1mmol), 50mL of water and 200mL of dioxane into a reaction bottle, heating to 120 ℃ for reaction for 6h, monitoring the reaction completion by TLC, adding water and dichloromethane after cooling, separating an organic phase, concentrating, and purifying by column chromatography to obtain a compound D72.
Synthesis example 10:
synthesis of Compound B2
Figure BDA0002426106780000321
Adding 1-chloro-5H benzo [ B ] carbazole (10mmol), 2-chloro-4-phenylquinazoline (10mmol), potassium carbonate (20mmol) and DMF200mL into a reaction bottle, heating to 150 ℃ for reaction for 4H, monitoring by TLC to complete reaction, cooling, adding water, filtering and drying to obtain B2-1.
Adding B2-1(6mmol), S2(6mmol), sodium tert-butoxide (10mmol), tris (dibenzylideneacetone) dipalladium (0.1mmol), tri-tert-butylphosphine (0.2mmol) and 150mL of xylene into a reaction bottle, heating to 150 ℃ for reacting for 8h, monitoring the reaction by TLC, cooling, adding water and dichloromethane, separating an organic phase, concentrating, and purifying by column chromatography to obtain the compound B2.
Synthesis example 11:
synthesis of Compound E17
Figure BDA0002426106780000322
Adding 3-bromo-5H benzo [ b ] carbazole (10mmol), 2-chloro-3-phenyl quinoxaline (10mmol), potassium carbonate (20mmol) and DMF200mL into a reaction flask, heating to 150 ℃ for reaction for 4H, monitoring by TLC to complete the reaction, cooling, adding into water, filtering and drying to obtain E17-1.
Adding E17-1(6mmol), diphenylamine (6mmol), sodium tert-butoxide (10mmol), tris (dibenzylideneacetone) dipalladium (0.1mmol), tri-tert-butylphosphine (0.2mmol) and 150mL of xylene into a reaction bottle, heating to 120 ℃ for reaction for 5h, monitoring the reaction by TLC (thin layer chromatography), cooling, adding water and dichloromethane, separating an organic phase, concentrating, and purifying by column chromatography to obtain a compound E17.
The present invention exemplarily provides specific synthetic methods for the above compounds, and compounds for which specific synthetic methods are not given in the following examples are also prepared by similar methods, and can be obtained only by replacing raw materials, which are not described herein again, or can be prepared by other methods in the prior art by those skilled in the art.
To verify the certainty of the molecular structure of the compound of formula I used in the examples of the present invention, we confirmed it by elemental analysis (seimer fly FLASH 2000CHNS/O organic element analyzer) and mass spectrometry information (ZAB-HS type mass spectrometer manufactured by Micromass corporation, uk), with the results shown in table 1.
Table 1:
compound (I) Elemental analysis (%) Mass spectrum (M/Z)
A1 C,85.70；H,4.78；N,9.52 588.23
A25 C,86.70；H,4.84；N,8.46 664.26
A33 C,87.53；H,4.91；N,7.56 740.29
B2 C,86.71；H,4.84；N,8.45 664.26
C2 C,86.70；H,4.86；N,8.44 664.26
C25 C,86.70；H,4.86；N,8.44 664.26
D1 C,85.66；H,4.80；N,9.54 588.23
D21 C,86.69；H,4.86；N,8.45 664.26
D26 C,86.71；H,4.84；N,8.45 664.26
D72 C,87.38；H,4.77；N,7.85 714.28
E17 C,85.70；H,4.78；N,9.52 588.23
Device example 1
The embodiment provides an organic electroluminescent device, and the specific preparation method is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the ITO anode in a vacuum chamber, and vacuumizing to<1×10-5Pa, vacuum thermal evaporation of 10nm HT-4: HI-3(97/3, w/w) mixture as hole injection layer on the anode layer film in sequence, 60nmThe compound HT-4 is used as a hole transport layer, the compound A1: RPD-8(100:3, w/w) with the thickness of 40nm is used as a light emitting layer, the compound ET-46: ET-57(50/50, w/w) mixture with the thickness of 25nm is used as an electron transport layer, LiF with the thickness of 1nm is used as an electron injection layer, and metallic aluminum with the thickness of 150nm is used as a cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
Device examples 2 to 11, comparative examples 1 to 3 differ from device example 1 only in that the light-emitting layer host material a1 was replaced with the light-emitting layer host material shown in table 2.
The structure of the host material of the luminescent layer in the comparative examples 1 to 3 is as follows:
Figure BDA0002426106780000341
and (3) performance testing:
(1) the organic electroluminescent devices prepared in examples and comparative examples were measured for driving voltage and current efficiency and lifetime of the devices at the same luminance using a PR 750 type photoradiometer of Photo Research, a ST-86LA type luminance meter (photoelectric instrument factory of university of beijing), and a Keithley4200 test system. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 3000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the current efficiency of comparative example 1 was taken as 1, and the remainder was the ratio to the current efficiency of comparative example 1.
The results of the performance tests are shown in table 2.
Table 2:
Figure BDA0002426106780000342
Figure BDA0002426106780000351
the results in table 2 show that the novel organic materials of the present invention are useful for organic electroluminescent devices, resulting in devices having both lower driving voltage and higher current efficiency.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (10)

1. A compound of the general formula I:
Figure FDA0002426106770000011
in formula I: l is1And L2Each independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
Ar2and Ar3Each independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
R1and R2Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar1is of the formula a1:
Figure FDA0002426106770000012
in formula a1: x1-X8Selected from the group consisting of CR3Or N, R3Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, two adjacent R groups3Can be fused into a ring;
when the substituent group exists in the groups, the substituent group is selected from one or the combination of at least two of halogen, cyano, carbonyl, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 monocyclic aryl or condensed ring aryl, C3-C30 monocyclic heteroaryl or condensed ring heteroaryl.
2. The compound of claim 1, having the structure of formula i-1, i-2 or i-3:
Figure FDA0002426106770000021
in the formulae I-1, I-2 and I-3, L1、L2、Ar1、Ar2、Ar3、R1And R2Are as defined in formula I.
3. The compound of claim 1 or 2, Ar1Selected from the structures of formula a1-1 or a1-2 as follows:
Figure FDA0002426106770000022
in formulas a1-1 and a1-2, the X3-X8Is as defined in formula a 1;
preferably, X is3-X8Are both CH.
4. The compound of claim 1 or 2, Ar1Selected from the structures of formula a1-3 or a1-4 as follows:
Figure FDA0002426106770000023
in the formulas a1-3 and a1-4, R3And X3-X6Is as defined in formula a 1;
preferably, X is3-X6Are both CH.
5. A compound according to any one of claims 4, wherein R is3Selected from the group consisting of substituted or unsubstituted structural formulas:
Figure FDA0002426106770000031
6. the compound of claim 1 or 2, wherein in formula i, i-1, i-2 or i-3:
L1selected from a single bond or one of the following substituted or unsubstituted groups: phenylene, naphthylene, pyridylene, biphenylene;
L2selected from a single bond or one of the following substituted or unsubstituted groups: phenylene, naphthylene, pyridylene, biphenylene, dibenzofuran, dibenzothiophene;
Ar2and Ar3Each independently selected from one of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, dibenzofuran, dibenzothiophene, carbazolyl.
7. The compound of any one of claims 1-6, wherein R1、R2And R3Each independently selected from hydrogen or the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, etc., p-o, etc Dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidyl, benzopyrimidinyl, quinoxalyl, 1, 5-diazaanthracenyl, 2, 7-diazpyrenyl group, 2, 3-diazpyrenyl group, 1, 6-diazpyrenyl group, 1, 8-diazpyrenyl group, 4, 5-diazenyl group, 4,5,9, 10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl groupOne of or a combination selected from the group consisting of oxadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl;
preferably, said R is1And R2Each independently selected from hydrogen.
8. The compound of claim 1, selected from the compounds of the following structures:
Figure FDA0002426106770000041
Figure FDA0002426106770000051
Figure FDA0002426106770000061
Figure FDA0002426106770000071
Figure FDA0002426106770000081
Figure FDA0002426106770000091
Figure FDA0002426106770000101
Figure FDA0002426106770000111
Figure FDA0002426106770000121
Figure FDA0002426106770000131
Figure FDA0002426106770000141
Figure FDA0002426106770000151
Figure FDA0002426106770000161
Figure FDA0002426106770000171
Figure FDA0002426106770000181
Figure FDA0002426106770000191
9. use of a compound as claimed in any one of claims 1 to 8 as a material in the light-emitting layer in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the compound according to any one of claims 1 to 8;
preferably, the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, the hole injection transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is arranged between the hole transport region and the electron transport region; wherein the light-emitting layer contains the compound according to any one of claims 1 to 8.
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CN114516861B (en) * 2022-03-15 2023-09-22 上海八亿时空先进材料有限公司 Carbazole derivative, organic electroluminescent element, display device, and lighting device
CN114957094A (en) * 2022-06-09 2022-08-30 北京八亿时空液晶科技股份有限公司 Polysubstituted carbazole derivative and application thereof

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